6273-82-1Relevant academic research and scientific papers
Aruncin B: Synthetic Studies, Structural Reassignment and Biological Evaluation
Ribaucourt, Aubert,Towers, Christopher,Josa-Culleré, Laia,Willenbrock, Frances,Thompson, Amber L.,Hodgson, David M.
supporting information, p. 16525 - 16534 (2017/11/14)
A ring-closing alkene metathesis (RCM)/ oxyselenation-selenoxide elimination sequence was established to the sodium salts E- and Z-25 of the originally proposed structure for the recently isolated cytotoxin aruncin B (1), as well as to the sodium salt Z-34 of a related ethyl ether regioisomer; however, none of their corresponding free acids could be obtained. Their acid sensitivity, together with detailed analysis of the spectroscopic data indicated that profound structural revision was necessary. This led to reassignment of aruncin B as a Z-γ-alkylidenebutenolide Z-36. Although a related RCM/ oxyselenation-selenoxide elimination sequence was used to confirm the γ-alkylidenebutenolide motif, a β-iodo Morita-Baylis–Hillman reaction/ Sonogashira cross-coupling-5-exo-dig lactonisation sequence was subsequently developed, due to its brevity and flexibility for diversification. Aruncin B (36), together with 14 γ-alkylidenebutenolide analogues, were generated for biological evaluation.
SYNTHESE ET REACTIONS DE DIELS-ALDER DES 5-ALCENYL (3H)FURAN-2-ONES
Alexandre, C.,Bertho, C.,Tabti, B.,Rouessac, F.
, p. 5481 - 5490 (2007/10/02)
Treatment of (5H)-2-furanones with LDA gives the corresponding (3H)-2-furanones which react easily in water with dienophiles to give cycloadducts in good yields and high stereoselectivity.
METHYL 3-PHENYLSULPHONYL ORTHOPROPIONATE: AN EFFICIENT REAGENT FOR THE SYNTHESIS OF γ-LACTONES AND BUTENOLIDES
Carretero, Juan Carlos,Lombaert, Stephane De,Ghosez, Leon
, p. 2135 - 2138 (2007/10/02)
Treatment of methyl 3-phenylsulphonyl orthopropionate with n-BuLi gives the corresponding carbanion which reacts with aldehydes or ketones to yield β-phenylsulphonyl-γ-lactones.Base-catalysed elimination yields α,β or β,γ-butenolides.
PREPARATION ET REACTIONS DE DIELS ET ALDER DES ALCENYL-5(3H)-FURANNONES-2
Alexandre, C.,Rouessac, F.,Tabti, B.
, p. 5453 - 5456 (2007/10/02)
Isomerization of readily available 5-alkenyl 2-(5H)-furanones 1 generated from aldehydes and propiolate anion to 5-alkenyl 2-3(H)-furanones 2 by base treatment provides a new and convenient access by mild Diels-Alder reaction in water to substituted cyclo
